Darn You Dean!
by arielbelle
Summary: Set in the future (roughly after the finale), Rory is back in town, and so is Dean. A friendly (and nervous) meeting might hold a new beginning to their complicated relationship. Will Rory and Dean get together? Will Dean's drinking and dark past affect the outcome? Will Rory's new path in life be set in stone? Rated M for language and [later] sexual content.
1. Chapter 1 - The Road Block

I am not affiliated with Gilmore Girls. *First fan fic, please be gentle with me :)

Rated M for language and [later] sexual content.

**Chapter 1:**

"Damn it!" Dean Forrester swore, his head bent over his new-to-him mustang. It was a bit older, but there was no reason in selling him a messed up car. Shaking his head, he backed up; tossing the tool he had been trying to use to tighten up a bolt at the engine. It bounced off and harmlessly hit the ground. He rolled his eyes and sat down on the curb in front of his parent's house. Living in Stars Hollow after everything that had happened seemed like a stupid move. He still couldn't believe he lived there himself. It wasn't that he didn't want to live somewhere else. He did. But he couldn't leave his hometown. The one time he had tried, he'd ended up on a five-day drinking binge and wound up in a detox center, being forced through AA. He didn't need that again; nor was he normally a drunk. It had been a horrible couple of years though. He forced a smile at the elderly couple watching him as they passed by. It wasn't their fault he was mad. He got back up, wiping the smudged grease from his hands onto his jeans. Oh well, he could buy new jeans.

It was kismet. There was no other explanation. There she was, walking across the road to Luke's. She had graduated college and gone off to this amazing job in New York or some big city. And yet here she was, in her sweats with her hair pulled up in a ponytail. Only Rory Gilmore could make frumpy look good. She glanced back, but Dean was only sneaking a peak at her. He'd gone back to "looking at his car". He didn't want her to think he was gawking at her. He only half smiled at the engine when he heard someone walking over.

"Hey there." She said, her voice sounding to Dean just like an angel.

"Hey Rory." He said with a smile on his face. His eyes searched hers as she looked back at him.

"Nice car." She said, inspecting the blue car. "The white stripes are a nice touch." She said, smiling a bit. Dean smiled back.

"I know, but the car itself isn't so nice. I am not exactly sure what's wrong with it." He admitted, rocking back on his heel. "But I'm sure you wouldn't want to hear about my theories."

She laughed and he caught his breath. "Well… you know me too well." She smirked, looking over towards Luke's. "I have to go meet my mom. But is there any way we could have lunch later? We could go to Al's Pancake World for some Chinese food…" She offered, her voice shaking just a bit as if she were nervous.

"Sure, I'd love that." He replied, shoving his hands into his pants pocket to hide the shaking.

She started walking away, looked back and said "Five thirty?" He nodded.

"Sure." He replied. She grinned once more at him and disappeared into Luke's.

_I can't believe she wants to have dinner. _Dean thought, after he showered a little while later. His hair was in dire need of a cut, but at least it wasn't too unruly. He tried to comb it but gave up as it curled outward. He hadn't ever cared too much about his hair; now wasn't really the time to worry about it. Dean headed out the door at 5:15; he lived just a block away from Al's but he needed to be just a bit early. Rory was a complete perfectionist; she was either right on time or early. She had never been late for anything like that except for the brief time she dated Jess. He felt a slight pang in his chest; even after all this time it still hurt to think about her and Jess. He shrugged it off. They had both grown up. Plus Rory had lost her virginity to Dean; Jess couldn't possibly hold a candle to him. _Wait, could he?_ Dean thought, trying desperately to put these thoughts behind him as he walked. He entered Al's and found a seat by the window. The restaurant smelled horrible, because all of the mixed food smells. Dean laughed at himself and put the weird looking menu by the window. He already knew what they would order: Every single type of Chinese food that Al had.

Rory entered the restaurant and noticed Dean automatically. She moved over to him. Dean's heart was going crazy in his chest. He smiled and she smiled back. She leaned down and kissed his cheek, then took the seat across from him.

"Hi." She said. He replied with, "Hey beautiful." She blushed. "How have things been?" She asked, and he studied her face. He wasn't the type to lie, but he thought about it for a moment, and then went on with what he would say.

"Things haven't been too good. But things are looking up now." He meant because of Rory but it was true about everything else too. He had a new stable job as an architect's assistant, was back in school to be an architect. The owner of the company he worked for was paying for his schooling, that way they could go into business together. They had been friends for years and it seemed like a great thing. He was very excited and proud of this. He told Rory all this, but also told her some about the past.

"Things haven't been the easiest recently, mainly because after things happened with us, things went downhill. I quit eating, I quit living really." His voice was shaking, from raw emotion and from not knowing how she would react to what he was going to tell her. "I moved away for a bit, because I thought maybe it would help. But I also lost my family when I moved; none of them would talk to me. They all thought I was being stupid. Clara especially thought so." He bit his lip for a second. "I became an alcoholic. I lived away for a year. Give or take. I drank myself into a horrible depression. After drinking 5 or more days straight, my family came to make sure I was alive. And what they found wasn't much better. They saw that I was in horrible shape and forced me to go to Rehab. I spent 9 months in detox and learning better ways to cope with my issues. I have been almost a year sober." He said rather proudly at the end, but still felt like maybe she'd run now.

"Oh Dean, I'm so sorry." She said, biting her lip now. Dean could see that he'd upset her. That was the last thing he'd wanted to do; he hadn't told her for her to feel responsible or for her to pity him. He owed her the truth and not some sugar-coated bullshit.

"I'm sorry." He said, reaching out to touch her hand. She smiled a weak smile.

"I didn't realize things had been so tough for you. I'm in town for a similar reason. Not the alcoholic thing, but because I failed at something. I completely bombed out on my job. I don't even want to be a journalist anymore." She admitted, and Dean felt a pull of sadness for her. She must have been really confused and sad. "I didn't have it in me anymore. And so I moved back home. I know Stars Hollow doesn't hold too much for my future but I think I'm going to teach." She said a small smile on her face. "Four more years of school and I'll be a full time teacher. In the meantime, I have a job at the elementary school as a substitute. Also, they accepted my request to work part time as a librarian when I'm not subbing." She seemed more than thrilled at this prospect, and Dean felt genuinely happy for Rory.

"That's great!" He said. He could picture Rory working at a school. He couldn't exactly picture her with kindergarteners but maybe a little older.

As if on cue, Lindsey walked into Al's Pancake World. It was as if this was destined to be a road block; Lindsey _never_ ate at Al's.

Dean ducked and whispered "I will be right back…" He glanced at Lindsey and ducked into the dinky bathroom. It was the last thing Dean needed; a confrontation with Lindsey in front of Rory; or for Lindsey to decide to confront Rory about her and Dean's indiscretion. He leaned up against the wall, more for support than anything. He texted Rory _has she left yet?_ Rory replied a moment later with _No._ Dean frantically tried to calm his heart. This meeting with Rory was supposed to be a good thing. Not an all-out war. _Is she getting a table or just take-out?_ He never got a reply back. He waited for a moment, but then peeked out the door. Lindsey was gone, but so was Rory. Dean cursed himself as he dropped his phone in his pocket and walked out the door. He looked around, finally spotting Rory's car. He walked towards it, but was only interrupted by Lindsey. He swore out loud, glancing at Lindsey.

"I have nothing to say Lindsey. Go away." He demanded, his voice very callous. It wasn't her fault; none of this was. That made everything so much harder. As Rory's car passed, Dean saw the mild look of hurt and alarm in her eyes. His heart dropped. Without a word to Lindsey, he walked back to his parents house.


	2. May The Force Be With You

Chapter 2:

Rory felt absolutely humiliated. She'd gone out of her way to meet with Dean and Lindsey showed up. She parked her car in front of her mother's house, barely glancing as Luke Danes shoveled the walk.

"Luke, it's not icy out." She said, stopping for a second to peer at the work he'd done to the sidewalk.

"Not yet." Luke said, shoveling some more salt onto the pavement, glancing around at the work he'd done already.

It's not even supposed to snow or get icy." She said, and Luke shrugged.

"TV says otherwise." He said, looking at the sky. Leaving Luke to his work, she moved on through the house. The only reason she didn't question what Luke was doing more than she had was because she knew that he was just trying to get away from her mom.

"Mom?" Rory called out, looking everywhere for her mom. She paused at the kitchen table and opened up the box of poptarts. In the box all she found was an empty wrapper. She threw the box in the trash.

"You ate the last poptart!" She yelled, disappearing into her bedroom. It was still neat and tidy, just the way she had left it. It felt strange to be living at home again, but it felt right at the same time. The only thing that seemed to feel wrong about it was her mom's relationship with Luke. By wrong, Rory just meant different. She loved Luke but ever since the fiasco with Lorelai marrying Rory's dad Christopher, Rory couldn't imagine her mom getting remarried, again.

"I ate the last one. I don't regret it." Her mom said as she flounced into the bedroom, sitting down on the bed. "I ate every last little crumb and it was ah-maazing." Lorelai said, a smirk on her face.

"Yeah yeah." Rory retorted, pushing the book she had glanced at backwards on her desk. The pile of books placed precariously on the desk teetered for a moment but didn't fall. Satisfied, Rory began to unpack. "So you know Luke's putting salt on the sidewalk right?" She asked, glancing at her mother through her mirror.

Lorelai shrugged. "He can't quite get used to this." She said, pointing towards her bulging stomach. "It must be hard on him; he's never been pregnant before."

"I should hope not." Rory said, folding up a sweater and placing it in her dresser. "Imagine if he actually had to go through it." She said kind of sadly, more so than she would have wanted.

"What's wrong?" Lorelai asked her voice full of concern. All of a sudden something had changed in her daughter, and she couldn't catch up on it quickly enough for her liking.

"Just… well, it's kind of silly. But I went on a date with Dean. Well it was more like a dinner. But I had initially wanted it to be a date." She said, thinking her words out carefully. Her pregnant mom didn't necessarily need all the extra details. But she told her an abbreviated version. "I thought things would go well; it was just dinner at Al's Pancake World. He looked great, handsome and stuff. And he really got down to telling me the details of his past – which I imagine you know all of."

Smirking, Lorelai waved Rory along. "Yes and?"

"Well, then Lindsey came in." She said, trying not to show her disappointment.

"Oh no. She did? What did he do?" Lorelai asked, enjoying this more than she should have.

"Well he went to the bathroom and started texting me. Asking me if she'd left." She turned around, shoving her under garments into the top drawer. "And then she came over to me. She was a total bitch to me – I can't blame her for that – but then she told me I needed to watch out; that she and Dean still had something going on."

"Oh no, Rory! Do you believe her?" Lorelai asked, knowing now why her daughter was upset. She wasn't used to this; usually their witty banter and surprisingly interesting conversations entertained the masses – today though, her baby was hurting.

"Why shouldn't I? He even talked to her after he left the hiding spot." She said, dropping down next to her mom on the bed. "They seemed pretty cozy to me." She said, biting her lip. "I went totally out on a limb. It might have been impulsive but I truly loved Dean. I thought maybe he still felt the same. In fact, I still think he does. It was in his eyes. But apparently he can't quit with Lindsey. After so much Logan, I'm completely done with that kind of love."

"Be strong. May the force be with you." Her mom said, placing her hand over her chest. "Yoda I am, happy be me." She said, looking outraged as Rory rolled her eyes and left the room. "This is some of my best material!" Lorelai shouted as she heard the refrigerator opening.

**Please talk to me**_._ The text was something Rory kept reading over and over, trying to decipher it's meaning. Was he concerned or did Dean know that Rory knew about Lindsey? She shoved her phone back into her pocket. _Let him worry about it._


	3. Chapter 3: Fireworks

**Chapter 3:**

She wouldn't answer his text messages. If she saw him in town, she went the other way. It wasn't like Rory to be so strange around Dean. He couldn't figure out what had happened. Was it simply because he'd ducked and ran instead of being a man and facing Lindsey head on? He may not have handled it very well but he didn't want to fight with Lindsey in public in front of Rory. Or worse off, Lindsey fight with Rory in public. Dean struggled through work, hoping that it was going to be alright. That perhaps she'd message him back. Or that she'd come see him in person. Of course neither of these happened. Instead, he was miserable. Two weeks had passed and he couldn't get anything from her. He knew he had to confront her, but he didn't want to be the crazy stalker.

He bit the bullet about three days later. She had made the mistake of going into Luke's without her mom. And Luke had taken the day off for the OB appointment. It still seemed strange to Dean that Luke and Lorelai were having a baby together. They would find out the sex of the baby that day. Dean walked over to Rory's table. Before she could get up, Dean said, "Please Rory. Don't. Let me talk to you." He said, begging.

Rory glanced up at him. "Fine. You have until I finish my breakfast. Then I have to leave. So talk fast." Dean would take whatever he could get.

"I don't understand why you won't talk to me." He began, probably not choosing the best words. "But I know that it had something to do with Lindsey. She and I have been rocky and I know I should have stepped up and talked to her that day at Al's, but I thought I was protecting us both by ignoring the situation. I probably made things worse; for that I apologize." He finished, never breaking eye contact with Rory.

"Dean, you shouldn't have left me with her. But I'm glad you did. It's nice to know where things really stand. Though I have to say that you handled it badly. Why agree to come with me?" She said with her voice a bit louder than she'd intended, so naturally all of Luke's customers were very aware of the confrontation between Dean and Rory.

"Rory… I wanted to see you. I think of nothing but you." He admitted, feeling nervous and edgy and hopeful all at the same time.

"Then perhaps you should set your affairs in order first." With that, she pushed her chair back and dropped a twenty on the table. She shouted to Lane on her way out, "I'll get my money back later!"

Dean, dejected, sunk down in his chair.

Later:

"I'm ready to burst." Dean said, talking to a friend who he'd graduated school with. He met his friend's eyes and his friend shook his head.

"Are you ever going to be done with Rory, man?" He asked, his laid back hippie vibe cutting into Dean's brain. He tried to ward of the initial angry thoughts swimming in his head. Lyle's hippie phase hadn't been just a phase; it was ongoing. Dean shrugged it off.

"Are you ever going to be done with pot?" He retorted, being not-so-pleasant. He couldn't help it. He took out his phone and typed, **Please talk to me. I don't know what I did wrong.** He hit send, and then shoved it back in his pocket. He didn't want to grovel but he truly didn't understand what he'd done.

_**Ask Lindsey.**_ She replied. He paused, puzzled. What, did Lindsey talk to Rory? He sighed; of course she had. What had she said though? He texted Lindsey. **Meet me at the square.** He knew she would, so he didn't even frame it as a question.

He got an excited message back, and he walked to the square. It wasn't far from his parent's house. He sat down on a bench in the gazebo.

Lindsey was practically running in his direction. He rolled his eyes. He knew that she still held a candle for him but he was so over her. Dean put his head in his hands as he heard her squeal out.

"Dean! I'm so glad you called me!" She was so giddy it almost hurt him to be mad at her. He sighed.

"Lindsey, it's not a get-back-together meeting." He watched as her face fell. She almost looked to the point of crying.

"Then what is it." She asked, her voice flat. She looked at Dean, with hope still in her eyes.

"What did you tell Rory?" He demanded with his heart in his throat. He never wanted any of this, but apparently it was the only way he could find out what actually went on.

"Nothing." She said evasively. She looked guilty to Dean though.

"Tell me Lindsey." He said, standing up.

"I told her we are still together." She said, angry tears in her eyes. "It may not have been the truth, but it was worth it to see the look on that whore's face!" She said, getting up. "Damn You Dean! Why do you do this to me? With HER?" She shouted. Shaking his head, Dean started walking away.

"You owe me an answer! I will continue to mess up the relationship you're trying to foster with that hooker, and I won't stop. You married ME Dean." She yelled.

"I don't owe you anything Lindsey. She's not a whore, she's not a hooker. She is the one I'm in love with. I'm sorry you're so jealous that you can't see past your own little world. But we have been over for a long time. I don't want you back. I don't want you to interfere in my relationships because WE ARE NOTHING. I will tell Rory it is nothing but a jealous little girls' idea of what love was." Dean shook his head as he walked away.

He hated hurting Lindsey because he had been the bad guy this whole time. He cheated on Lindsey. She didn't deserve that. But he was trying to move on. He was trying to be a good guy. He couldn't keep Lindsey hanging on (with or without his input). Once she was out of sight, Dean dialed Rory's number. As predicted, she didn't answer the phone. Instead, he left a message.

"Rory, Lindsey designed what she told you to scare you off. She thinks we're still together even though I swear we have been nothing for a very long time. I told her to move on. Please don't believe what she said. I want YOU. I've always wanted you. I'm sorry if I hurt your feelings but there isn't a single thing going on between Lindsey and myself. Please, call or text me so we can get together."

Instead of waiting for her reply though, he walked over to Lorelai and Rory and Luke's house. Knocking on the door seemed like a bad idea, so instead Dean walked over to Rory's window and knocked. After a minute, she peeked out. He waved, and she pulled back. He wasn't sure if she was going to the door or not; until he heard the front door open and she stepped out.

"Dean." She said, her voice sounding kind of upset. He walked over to her.

"Rory, you have to know I wouldn't be with Lindsey. I want you. I've always wanted you. At first Lindsey was a distraction. Unfortunately for me though, I decided I'd never get you again and I married her. Then when we slept together, I really knew what I had done. I'd hurt her but I'd gotten the girl I'd always wanted. Then when we split, I felt dejected. I never wanted anyone as much as I have you. You're the girl for me, Rory Gilmore. Here's my third chance staring me in the face and I'm taking it. I'm all in." He stepped up onto the porch. He wrapped his arms around her and pulled her closer. With a deep meaningful look into each other's eyes, Dean leaned down and their lips met. A thousand fireworks went off in Dean's head. It looked to be the same way for Rory.

As they pulled away, Rory grabbed the cuff of Dean's button-down shirt. She smiled wryly and whispered, "Damn You Dean." She kissed him again, and his heart was so full it was about to burst.

"I love you Rory Gilmore." He said, looking into her beautiful eyes that held a thousand memories and words left unsaid.

"I love you Dean Forrester." She said, hugging him tight and leaning her head on his shoulder.


	4. UPDATE!

Author's Note: This fanfiction will be updated very soon! I don't want to lose them though, so here is a bump***

Thanks for reading!


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